A Jory Story
by quackquackduckstuck18
Summary: chpt. 1: Rory goes looking for a certain someone at Luke's and it begins to snow. Now a series of Jory oneshots Jess/Rory Co-written by @Spookyspookspook11
1. Chapter 1

After a long day at Chilton, Rory walks to Luke's in hopes of seeing a certain someone. She rushes into the little coffee shop, pulling her jacket up to shield her from the cold. Once inside, she scans the room hoping to see Jess, but instead she is greeted by Luke.

"Rory!" Luke calls from behind the counter. "How was school?" He asks while wiping down a coffee mug.

"Oh, fine." She replied still looking around quite obviously searching for Jess.

Luke smiles down at the mug and says quietly, "He's upstairs."

"Thank you," She says awkwardly, turning a bright shade of red and running behind the curtain and up the stairs. She stops outside the door at the top of the stairs, unsure of whether or not to knock or just walk in.

She knocks. "Jess! Can I come in?" She asks.

The door opens and Jess is standing there with a smirk on his face.

"Hey." He says, continuing to smirk.

"Hey." She says back.

"You can come in, ya know." He says STILL SMIRKING.

"Oh, yeah, alright." She says, a light shade of red creeping across her cheeks.

Jess backs up to let her in, closing the door behind her and walking over to the fridge where he takes out one of Luke's beers and offers it to her.

"No, thanks, you shouldn't be drinking that you know."

"Who's gonna stop me?"

"I am?" She says, uncertainly.

"Oh yeah?" Jess says while walking slowly towards her, the look superiority replaced with one of desire.

"Y-yeah." Rory stutters, backing away.

Her back hits the wall. He puts the drink on the counter and steps toward her. Her breath quickens. Jess' smirk is softer now but his expression is intense. She looks up at him and he takes her chin in his hands and-

The door flies open. Luke rushes in. The two pull apart like the parting of the Red Sea.

"You guys ok in here?" He asks suspiciously.

Rory nods quickly, color flushing her whole face. Jess gives him a look of frustration.

"Well, I came here to tell you guys, it's looking pretty bad out there. I think you should stay here with us Rory."

Rory looks over at Jess. The smirk is back.

"So Rory, you can sleep there, you got your pillows and clean sheets…" Luke says as he spreads a blanket out over the couch.

"Thank you Luke."

"Yup, I'm gonna just close up the diner and stuff…. Don't stand too close to each other… Jess, just… Stay on your side of the room." He says awkwardly. He heads towards the door but turns around before he's about to leave. "I don't wanna walk in on anything… read your books,"

Rory nods, blushing and Jess just raises his eyebrow and opens a book, but as soon as the door closes he puts it down.

"So, where were we?" He asks, moving to sit next to Rory on the air mattress that used to be his.

"W-well…" she stammers hoping to eventually get some words out.

"Well...how about…" He says, glancing at her lips between words.

The door opens again.

"Oh come on!" Jess shouts in exasperation.

"I thought I told you to stay on your side!" Luke roars. "Keep it up and you'll be sleeping in the closet pal."

Jess dramatically gets up and walks back over to his mattress, exaggerating each step.

"That's right. Now you stay there."

"Just go tend to your diner," Jess grumbles and Luke leaves hesitantly, keeping his eyes suspiciously on Jess.

"Luke can really be a buzzkill, huh?" Jess says.

"I mean, I guess. He's just looking out for us." Rory replies politely, even though she's also frustrated.

"I could lock the door…" Jess says with a wink.

"Jess, you can't lock your uncle out of his own apartment just because you want to kiss me." Rory says but then realizes what exactly she said and becomes embarrassed. "I mean I don't know if you wanted to kiss me, it just seemed like from the way you were acting and you kept getting really close and-" Jess cuts her off. His lips are on hers. Rory's mind goes blank except for the one thought that Jess smelled like a bookstore and she liked it. A lot.

Then suddenly The door is thrown open and Luke is standing in the doorway, spatula in hand.

"No. Off of her. Get back to your bed. Jess. I warned you. I knew this would happen. I could feel it. You two were not on your own sides of the room!" Luke says, frantically waving his spatula around, gesturing to Jess then to Rory then shooing Jess back to his own mattress with it.

"What would Lorelai think of this." He mutters to himself as he puts down the spatula and heads into the bathroom.

"See, real buzzkill."

"Jess, he just cares about us."

"Yeah well… Buzzkill."

"I can hear you!" Luke calls from the bathroom.

"That's the point!" Jess calls back, picking up his book as Luke comes out of the bathroom.

"Bedtime. Both of you." Luke says angrily.

"You gonna read us a bedtime story Uncle Luke?" Jess asks mockery written all over his face.

"You will get on that bed, and you will get on it now, or there will be consequences." Luke says, pushing Jess to his side.

"No fair! I didn't get my warm milk and cookies yet." Jess pouts, but lays down nonetheless. Rory is too stunned to move and when Luke tries to guide her to her own bed she flinches dramatically.

"Sorry Luke." She mutters, embarrassed.

"I know it wasn't your fault Rory." He says walking to his own area, preparing to turn off the lights. "Stay on your side, _Jess._" Luke says warningly.

From his side, Jess throws his hands up in surrender.

"Whatever."

Rory awakes to a tapping on her shoulders. She opens her eyes and finds Jess standing over her with a finger to his lips.

"What?" She says annoyedly.

"Come on."

"Come on where?"

"Surprise. Just follow me."

"What time is it?" Rory looks around for a clock, pushing herself into a sitting position.

"Doesn't matter, come on, we don't want to wake up Luke."

"Jess it's late and I was sleeping."

"And it's a friday and nice outside." Jess argues.

"It's snowing."

"Nice."

"Cold."

"You can have my coat."

"Fine."

Rory gets up as quietly as she can and follows Jess to the door. The two of them sneaking downstairs to the diner. Jess, it seems had been planning this, because he had a cup of coffee prepared which he hands to Rory then he offers her his jacket as he pulls on his hoodie.

"I have my own coat."

"Well if you change your mind… " He says, pulling the jacket on too.

Rory sips the coffee and Jess looks through the drawers behind the counter and pulls out a pack of cigarettes and a lighter, shoving them into his pocket. "Just in case" he says to her critical look.

"Jess, where are we going?" Rory asks again sipping the coffee.

"You really don't understand the meaning of the word 'surprise', do you?" He teases. "C'mon." He takes her hand and leads her out the door. He pulls her behind him, the snow fluttering all around them making for a very romantic scene. Jess knew this of course, which is probably why he decided to take her out in the first place.

"This way." He says as they cross the street to the gazebo.

"How is this a special surprise?" Asks Rory.

"Hey, I never said it was special." Jess replies.

"Well why are we here?" She asks, tired and fed up with his antics, although they could be so cute.

"Because Luke isn't." He says, the smirk returning once again.

"And what are you expecting to get out of this endeavor?" Rory teases.

"Hmm, maybe this.." He stops talking and pulls her closer and kisses her once again. It was freeing to be away from the prying eyes of Luke and everyone else in Stars Hollow. But just when they thought everything was perfect…

"JESS MARIANO WHAT THE HELL DID I TELL YOU?!"

Fin.


	2. Chapter 2

It was a warm day in Stars Hollow and Rory found herself reading a book outdoors in preparation for the upcoming picnic event. She was also waiting for her boyfriend who had planned to meet her there. However, he seemed to be running late. It was a surprise when she felt someone sit beside her on the bench, she turned, expecting Dean, but instead was looking into the eyes of Jess Mariano.  
"Hey." He said.

"Hey." Rory replied nervously.

Jess was Luke's nephew, and she had grown up around Luke, so staring into Jess's eyes shouldn't be as strangely endearing as it was. At first, Rory had been a bit annoyed to have Jess always showing up and trying to talk to her, but she reluctantly felt herself growing fond of him, as he was not the bad boy from New York as everyone thinks he is. He was smart - really smart. And she found herself wanting to discuss books with him constantly. It was the fact that he'd showed up now, while she was waiting for her boyfriend, that startled her. Especially since she knew that Dean wasn't particularly fond of him. At all. Intense hatred would be the best way to describe Dean's feelings for Jess.

"So, what brought you here on this hot and sweaty day?" Jess says, draping his arm behind her. Rory shifts away a bit, but doesn't completely object.

"Waiting for my _boyfriend,_" she tells him. Jess is disappointed but he tries to play it off cool.

"Right. _Dean. The wonderful boyfriend_." He says, withdrawing his arm.

"That's right." Rory replied, giving him a slight smile. "Are you going to participate?"

"What?" Jess asks. (obviously not planning on participating)

"The picnic raffle." Rory says, gesturing to the gazebo behind her, where townsfolk were putting up a large banner reading "Picnic Day."

"Oh that." He says, thinking. "I think I might." He says finally, smirking at her.

"You definitely should, there are some really good baskets out there." She smiled, completely oblivious to what he was implying.

"I'm sure there are." He says still smirking.

"What's that face for?" She asks, smiling.

"What face?"

"That smirky look, like '_I'm Jess Mariano and I know something you don't'"_ She imitates him in an unrealistically deep voice.

"I don't sound like that, and it's not '_smirky'"_ He says.

"Oh, sure you do." Rory giggles.

Dean chooses that moment to walk up behind them.

"Oh, hey Dean." Rory smiles at him.

They kiss and Jess is still sitting there, smirking.

"Hey Rory." He smiles at her, completely ignoring Jess as he sits down. "I got the money to buy your basket." He says.

"Oh great!" She says.

"So Rory, any recommendations on whose basket I should buy?" Jess talks over Dean.

"Oh, Sookie is an amazing chef, although Jackson is supposed to bid on hers. There are plenty of nice baskets, I think it's worth a shot." She says before turning back to Dean.

"Huh, Ok, well, you two have fun doing whatever it is you two are doing. I've gotta go steal some money." Jess says. Then at Dean and Rory's scandalized looks he sighs, "I'm joking, I'll ask if I can borrow it first."

Jess walks away and Rory watches him leave, Dean noticing that her attention is on Jess rather than him, he put his arm around her shoulders.

"Hey, we can get going now if you want." Dean says.

"Sounds good." Rory says distantly, her gaze lingering on Jess.

…

The next day, the auction begins. Lorelai had somehow convinced Luke to bid on her basket to avoid Miss Patty's attempts to set her up. Kirk had managed to win Sookie's basket, much to her dismay. Finally, the time came for Rory's basket. She scanned the crowd for Dean. He caught her eye and smiled at her, holding up the money he brought. She gave him a thumbs up and a smile before noticing Jess standing in the back. She made her way through the crowd and stopped in front of him.  
"Jess, glad you came, who's basket are you bidding on?" Rory said quickly and blushing because she had a sneaking suspicion it'd be hers.

"It's a surprise." He said, smiling.

Just then, Taylor decided to start the bidding.

To start there were a few other random guys who bid, but eventually they caught on that she was with Dean and, luckily, backed off. However, just as Taylor was about to declare Dean the highest bidder and winner of Rory's basket, another voice called out a bid.

"200 dollars!" Rory turns around and sees Jess holding up his hand. She tries to catch his eye but he won't look at her. Dean looks panicked and Rory looks at him apologetically and hopes he will understand.

Rory storms through the crowd to get to Jess, who had just claimed the basket.

"What was that?" She asks, crossing her arms.

"You said I should participate, so I did." Jess replied, taking a look inside the basket.

"Jess, you knew Dean was going to bid on my basket." Rory said, frustrated.

"So I did, I figured it'd be a nice little surprise for him." Jess says with a smile. "Shall we?"

"I need to talk to Dean first." Rory, sighed and then walked off.

Jess smiled down at the basket, very happy with his purchase.

…..

Rory walked up to Dean who was pacing back and forth, muttering something to himself. As soon as he noticed Rory, he looked up with an expression of pure exasperation.

"Rory, I swear, if you don't let me punch that guy.." Dean started.

"Don't worry about him. You know I wasn't planning on this right?" A look of panic crosses Deans face at that possibility but then he sighs and nods his head.

"I know, I know. It was him."

"I'm sorry. He's… He's-" But Rory can't find a word that describes Jess, so she just sighs.

"An idiot? Asshole? Rude?" Dean suggests.

"Yeah."

"You don't need to actually have lunch with him you know?" Dean says and Rory smiles at him sadly.

"Dean, it's tradition."

"Screw tradition." he shouts angrily.

"I'm sorry Dean. He has the basket, he payed for it."

"It was my basket though."

"I know, and you can take pleasure in the fact that he won't enjoy whatever crappy food I stuffed in there."

"Right."

"_You_ are my boyfriend Dean."

"I know. But he doesn't seem to care about that."

"But _I _do!" Dean sighs and runs his hand through his hair. After a few minutes he looks at Rory.

"I love you." He says hopefully.

"Love you too." Rory confirms softly.

"Right, well, you might have to make me another lunch tomorrow then." Dean laughs and so does Rory.

"I will!" She kisses Deans cheek and runs off towards the direction of the bridge and the creek.

When she gets to the bridge, Jess is sitting there, feet dangling off the edge, looking thoughtfully out over the water. She eases herself down beside him and looks out across the water as well.

"Hey."

"Hey."

"I'm sorry, I just have to know, why did you do it?" Rory asked.

"What?"

"You knew Dean would bid on my basket, didn't you?"

"Yes."

"So why would you also bid on my basket? When I said participate, I didn't mean start a fight between me and my boyfriend." Rory huffed.

"I figured Dean could use some healthy competition." Jess said beginning to unload the contents of the basket.

"Well, just know you're getting what you deserve, those are all Dean's favorites and I don't think you'll like them." Rory challenged crossing her arms.

Jess pulls out something that looks remotely like tuna salad and opens it, preparing to eat.

"What is this?" He asks, chewing and making a face. "This is disgusting."

"Well, that was a prank, and Dean wouldn't have fallen for it." Rory says, giggling.

"Are you kidding me?" Jess asks, spitting it into the lake.

"Nope. You know, for someone who outbid my boyfriend, you're kind of gullible."

"Oh really?" Jess says looking over, thoughtfully.

"Yes."

"Hmm."

"What?" Rory asks, noticing the strange look gracing his features.

"Do you want to know what I think?" Asks Jess, not waiting for answer before continuing. "I think that someone as smart as you can do better than some bonehead like Dean."

"Oh yeah? Know any eligible young men?" Rory replies, rolling her eyes.

"I can think of one…" Jess says, moving closer to Rory.

"Yeah? Who?"

"Dark hair, leather jackets, awesome."

"Hm… I can't recall anyone that fits that description…" Rory teases.

"Huh… that's odd. He actually knows about decent music and books and knows about the things you're interested in. I think you would like him."

"Would I now?"

"You would." Jess smirks at her.

"Well sucks for him, 'cause I love Dean." Rory says turning back to her food.

Jess's face changes from "smirky" to soft and serious.

"Rory, Dean is great, but he's sheltered. He is never going to get out of this town. You are going to go to college and become someone important and he is going to be here. In this small town, doing whatever it is he'll do while holding you back."

"Jess we aren't getting married!" Rory laughs.

"Well you're young! You should experience things. Get out of your comfort zone. Travel a bit. And with Dean you'll convince yourself that you're fine staying here. But you'll regret it later. You'll want to have known something other than this little town and it's stupid traditions and your daft boyfriend."

"Jess what is your problem?"

"My problem is that I like you. And I want to take you places, explore with you. I like you and you're in love with-with _Dean."_ Jess grumbles. Rory looks down. She doesn't know how to respond to that.

Of course she likes him back. There was that little bit of interest from the beginning. That small part of her that was intrigued by Jess and his chaos. And she had thrown that off. Convinced herself that it was nothing. Because she had Dean and he made her feel safe, and loved. And because Jess was trouble and he couldn't be trusted. But the fact was… Jess isn't completely trouble. He's smart and intellectual and interesting. He likes books and good movies and is funny. And he cares about her. Suddenly realization dawned on her. How would she be able to continue dating Dean while knowing she had feelings for someone else?

"I, uh, have to go." Rory gets up and walks away, leaving Jess alone on the bridge. But not for long. She was going to break up with Dean.


End file.
